Hydrochloric Acid → 5-Amino-1,3,4-trimethyl pyrazole hydrochloride

HRID 224820Notes

Reaction equation

HRID 224820 reaction equation
[CH3:1][CH:2]([C:5](=O)[CH3:6])[C:3]#[N:4].C(O)C.[CH3:11][NH:12][NH2:13].[ClH:14]>O>[ClH:14].[NH2:4][C:3]1[N:12]([CH3:11])[N:13]=[C:5]([CH3:6])[C:2]=1[CH3:1]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 702EthanolHCID 6061MethylhydrazineHCID 5369052-Methyl-3-oxobutanenitrile

Product 1

HCID 233305165-Amino-1,3,4-trimethyl pyrazole hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Methyl-3-keto-butyronitrile (J. Am. Chem. Soc. 79, 723, 1957) (25.25 g.) in 120 ml. ethanol was treated with 15 g. methylhydrazine while cooling. The solution was refluxed 3 hours then concentrated in vacuum, benzene added and the solution concentrated again. Ether was added to give 29.12 g. mp 70-106 of base (contained H2O). This was converted to the hydrochloride with HCl in isopropyl alcohol. HCl had mp 286°-288°.

Workup

  1. temperatureThe solution was refluxed 3 hours
  2. concentrationthen concentrated in vacuum, benzene
  3. additionadded
  4. concentrationthe solution concentrated again
  5. additionEther was added
  6. customto give 29.12 g

Sources & evidence

ORD record
ord-d0589c32ef3e44d3a284b33a207f2ca3
Source dataset
uspto-grants-1980_11
Patent number
US04234594

Reaction notes

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